190583-85-8

Upstream product

• 100-39-0 benzyl bromide 
• 51885-64-4 1,2-O-isopropylidene-β-L-arabinofuranose 
• 100-44-7 benzyl chloride 
• 532-20-7 L-arabinose 
• 103763-12-8 5-O-tert-butyldiphenylsilyl-α,β-L-arabinofuranose 
• 103763-14-0 (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol 
• 70057-97-5 6-hydroxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 
• 10368-86-2 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 

Downstream Products

• 339091-38-2 methyl 3,5-di-O-benzyl-L-arabinofuranoside 
• 162303-23-3 methyl 3,5-di-O-benzyl-α-L-arabinofuranoside 
• 1038922-15-4 C₁₉H₂₀O₅ 
• 442514-57-0 1-O-methyl-2-deoxy-2-fluoro-L-arabinofuranoside 
• 622785-69-7 1-((2S,3S,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 190583-99-4 1-((2S,3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 190584-00-0 1'-(3',5'-di-O-benzyl-β-L-ribofuranosyl)uracil 

Relevant academic research and scientific papers

L-nucleoside compounds and application thereof

The invention discloses L-nucleoside compounds having the structure characteristic represented by the formula (I) or pharmaceutically acceptable salts thereof, and belongs to the technical field of pharmaceutical chemistry. The compounds can inhibit the activity of RNA viral polymerase, so the compounds can be used as potential drugs for prevention and treatment of infection of RNA viruses such as HCV, influenza virus, HRV (rhinovirus), RSV, Ebola virus, dengue virus, intestinal virus and the like.

Oxetane amino acids: synthesis of tetrameric and hexameric carbopeptoids derived from l-ribo 4-(aminomethyl)-oxetan-2-carboxylic acid

The synthesis of methyl 2,4-anhydro-5-azido-3-O-benzyl-5-deoxy-l-ribonate, a δ-2,4-cis-oxetane-azido ester scaffold derived from l-arabinose, is reported. Iterative coupling methods were utilised to form homo-oligomers up to the hexamer in order to investigate the secondary structural preferences of these systems.

2'-deoxy-L-nucleosides

This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH2, NHR′, or NR′R″Z is H, F, Cl, Br, I, CN, or NH2. R is hydrogen, halogen, lower alkyl of C1-C6 or aralkyl, NO2, NH2, NHR′, NR′R″, OH, OR, SH, SR, CN, CONH2, CSNH2, CO2H, CO2R′, CH2CO2H, CH2CO2R′, CH═CHR, CH2CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C1-C6. R13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides

Using an inexpensive D-galactose from the chiral pool, L-deoxyribose, L-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis of L-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-L-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis of L-ribose, the key step of inversion of the 2-hydroxy group in the same substrate was carried out by intramolecular SN2 tandem reaction. Then the L-ribosyl donors were submitted to glycosidations according to Vorbrüggen's conditions to give L-ribosides (L-uridine, L-5-fluorouridine, L-iodouridine, L-thymidine, L-puridine, L-adenosine and L-guanosine) in excellent yields.

A stereospecific synthesis of L-ribose and L-ribosides from D-galactose

An inexpensive D-galactose was converted into L-ribose and its derivatives via mild reaction conditions. The L-ribosyl donor was submitted to a glycosidation according to Vorbrüggen's conditions to give L-ribosides in high yields.

Syntheses and coupling reactions of 1,2-anhydro-3,5-di-O-benzyl-α-L-ribofuranose and 1,2-anhydro-5-O-benzyl-3-O-methyl-α-L-ribofuranose

1,2-Anhydro-3,5-di-O-benzyl-α-L-ribofuranose (7) and 1,2-anhydro-5-O-benzyl-3-O-methyl-α-L-ribofuranose (20) were synthesized from L-arabinose via the key intermediates 3,5-di-O-benzyl-2-O-tosyl-(5) and 5-O-benzyl-3-O-methyl-2-O-tosyl-L-arabinofuranose (1